I used to not have an issue syncing workouts and using them with my watch so this isn't a newbie issue :) I'm not exactly sure when it started, but it has been around a month now (so version 7.0/7.1 on the 935). I was hoping an update would fix it, but have had no luck.
For Garmin app, I'm using the Google Pixel 2 XL so Android (the app has an issue that before it wouldn't have a check mark on the workout that isn't synced, but mine all show check marks and then lights up when I hit the check mark again and then it goes through, but it doesn't sync to the watch).
But I've also tried using the web based Garmin Connect with Garmin Express from a PC (GE updated today and it didn't work before or after). I know I've seen others report success with that but I've not been able to replicate.